US4786666A - Epoxy compositions containing glycidyl ethers of fatty esters - Google Patents
Epoxy compositions containing glycidyl ethers of fatty esters Download PDFInfo
- Publication number
- US4786666A US4786666A US07/122,060 US12206087A US4786666A US 4786666 A US4786666 A US 4786666A US 12206087 A US12206087 A US 12206087A US 4786666 A US4786666 A US 4786666A
- Authority
- US
- United States
- Prior art keywords
- composition
- dihydric phenol
- acid
- weight
- diglycidyl ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
- C08G59/1472—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4292—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with monocarboxylic acids
Definitions
- the field of art to which this invention pertains is polymers derived from polyepoxide resins and fatty acids.
- Epoxy esters are well known compositions which have been used industrially and in home maintenance for many years.
- Epoxy esters are made by reacting a polymeric epoxy resin, which contains both epoxy groups and hydroxyl groups, with fatty acids.
- the polymeric epoxy resin is made "in situ" by the reaction of a low molecular weight diepoxide with a dihydric phenol.
- Epoxy esters are described in a large number of patents, examples of which are U.S. Pat. Nos. 2,456,408; 2,493,386; 2,698,308 and 3,247,136.
- the esters are usually dissolved in an organic solvent at a resin solids content of 50 weight percent or less. Due to environmental concerns, there is a continuing effort to decrease the amount of solvent released to the atmosphere by increasing the solids content of coating composition.
- This invention is directed to epoxy ester composition.
- this invention pertains to a modified epoxy ester composition.
- this invention relates to high solids epoxy ester coating compositions.
- the epoxy ester composition of this invention is the reaction product of (a) a diglycidyl ether of a dihydric phenol; (b) castor oil polyglycidyl ether; (c) a dihydric phenol; (d) a monocarboxylic fatty acid; and (e) a dimer acid.
- the diglycidyl ether of the dihydric phenol, the castor oil polyglycidyl ether and the dihydric phenol are reacted in such amounts that the sum of the epoxide equivalents of the diglycidyl ether of the dihydric phenol and the caster oil polyglycidyl ether and the phenolic equivalents of the dihydric phenol are in the ratio of about 2:1 to about 4:3.
- About 70 to about 80 percent of the epoxide equivalents are derived from the diglycidyl ether of the dihydric phenol with the remainder being derived from the castor oil polyglycidyl ether.
- the monocarboxylic fatty acid is present in the amount of about 26 to about 42 weight percent and the dimer acid is present in the amount of about 4 to about 8 weight percent, said weight percents being based on the total weight of the components referred to hereinabove.
- the diglycidyl ethers of dihydric phenols useful in this invention are well known in the art. These glycidyl ethers are made by reacting a dihydric phenol with epichlorohydrin, generally in excess, using caustic as the condensation and dehydrohalogenation agent.
- the dihydric phenols used in making the glycidyl ethers contain two phenolic hydroxyl groups and no other groups reactive under the conditions of reactions.
- dihydric phenols examples include resorcinol, dihydroxydiphenyl, dihydroxydiphenyl ether, dihydroxydiphenyl methane, dihydroxydiphenyl ethane, p,p'-dihydroxydiphenyl propane (or Bisphenol A as it is commonly called), p,p'-dihydroxydiphenyl sulfone and the like.
- diglycidyl ethers will have epoxide equivalent weights of about 120 to about 300.
- a preferred diglycidyl ether is the diglycidyl ether of Bisphenol A having an epoxide equivalent weight of about 180 to about 200.
- the castor oil polyglycidyl ether useful in this invention is the reaction product of castor oil and epichlorohydrin.
- Castor oil is a vegetable oil obtained from the seeds of the castor plant and is the triester of glycerl and substantially ricinoleic acid.
- Epichlorohydrin is reacted with the hydroxyl groups in the ricinoleic acid portion of the oil using a Lewis acid catalyst.
- the resulting chlorohydrin adduct is dihydrohalogenerated with caustic.
- Castor oil polyglycidyl ether is described in detail in U.S. Pat. No. 3,351,574, which is hereby incorporated by reference.
- Castor oil polyglycidyl ether useful in this invention has an epoxide equivalent weight of about 550 to about 700.
- dihydric phenols useful in this invention are those which are listed hereinbefore in the description of the diglycidyl ether of a dihydric phenol.
- the preferred dihydric phenol is Bisphenol A.
- the monocarboxylic fatty acids useful in this invention are aliphatic acids which contain from about 10 to about 22 carbon atoms.
- the acids can be saturated or unsaturated with one to three ethylenically unsaturated groups per molecule.
- examples of such acids are capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, linoleic acid, linolenic acid, eleostearic acid, licanic acid and erucic acid.
- Such acid are also named from the oils from which they are derived, such as coconut fatty acids, corn oil fatty acids, linseed fatty acids, soybean fatty acids, tall oil fatty acids and the like.
- Epoxy esters which are used to prepare coating composition which dry or cure by air oxidation, are made with unsaturated fatty acids.
- Coating compositions which are cured with crosslinkers, such as urea-formaldehyde and melamine-formaldehyde resins, are made from epoxy esters which contain less or no unsaturation in the fatty acid portion.
- Preferred fatty acids for use in this invention are tall oil fatty acids.
- the dimer acids useful in this invention are dimers of unsaturated fatty acids, such as linoleic acid, linolenic acid, eleostearic acid and the like. Such acids contain an average of about 20 to about 44 carbon atoms per molecule. Although referred to as dimer acids, the compounds are mixtures of dimers and trimers with a small amount of monomer. Generally, the mixture contains at least about 80 weight percent dimer acids and about 2 to about 5 weight percent monomer with the remainder being trimer. Dimer acids are described in U.S. Pat. No. 2,482,761 which is hereby incorporated by reference.
- the backbone epoxy resin which is esterified with the fatty acids is prepared by reacting the diglycidyl ether of the dihydric phenol and the castor oil polyglycidyl ether with a dihydric phenol in the equivalent ration of about 2 epoxide equivalents to one phenolic equivalent to about 4 epoxide equivalents to three phenolic equivalents.
- the epoxide equivalent weight of the backbone resin, if isolated, is about 500 to about 1200.
- a preferred epoxide equivalent weight is about 750 to about 900.
- the backbone epoxy resin is prepared by heating the components at temperature of about 350° F. to about 500° F. for a time sufficient for the reaction to be completed as determined by the epoxide equivalent weight compared it to the calculated value.
- Catalysts typically used in "upgrade” reactions i.e., the reaction of low molecular weight diepoxides with dihydric phenols to make higher molecular weight epoxides, are used in this reactin.
- Examples of such catalysts are lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, triphenylphosphine, the "onium”, “sulfonium” and “phosphonium” compounds, e.g., tetramethylammonium chloride, and the like. The use of these catalysts are well known to those skilled in the art.
- esterification catalysts e.g., sodium benzoate. Heating is conducted at a temperature of about 325° F. to about 550° F. to complete the esterification reaction.
- a small amount of organic solvent which forms an azeotrope with water is added. Any of the aliphatic or aromatic hydrocarbons can be used. A preferred solvent is xylene.
- the esterification reaction is conducted until the acid value measures less than 10.
- dimer acids are added and the esterification reaction is continued until the acid value is reduced to below 10, preferably 2.5.
- the amount of fatty monocarboxylic acid used in preparing the compositions is about 26 to about 42 weight percent based on the total weight of the composition.
- the amount of dimer acids used is about 4 to about 8 weight percent based on the total weight of the composition.
- Preferred amounts are about 30 to about 38 weight percent fatty monocarboxylic acid and about 5 to about 7 weight percent dimer acids.
- Solvent solutions of the epoxy esters of this invention are formulated into coating compositions. It has been found that these castor oil polyglycidyl ether modified epoxy esters of this invention can be formulated into coatings having high solids at application viscosities.
- the compositions of this invention can be supplied to formulators at solids contents as high as 80 percent with viscosities of less than Z on the Gardner-Holdt scale. These solids and viscosities allow formulators to make varnishes and paints with low amounts of volatile solvents which enable them to meet various environmental laws pertaining to solvent emissions.
- Solvents used with the epoxy esters of this invention are hydrocarbon solvents, e.g., toluene, xylene, and naphtha, alcohols, glycol ethers and ketones.
- a preferred solvent is xylene.
- compositions of this invention can be formulated into air-drying and baking varnishes and enamels.
- Air-drying compositions will contain driers such as cobalt and manganese naphthenate, which are well known in the art.
- Baking compositions can also contain driers as well as crosslinking additives, such as urea-formaldehyde and melamine-formaldehyde resins.
- paints and varnishes various other components, such as pigments, anti-skinning agents and anti-flooding compounds, can be added.
- Example 2 Using the same procedure described in Example 1, an epoxy ester, which contained no castor oil polyglycidyl ether modification, was made from 43.21 parts of the diglycidyl ether of Bisphenol A described in Example 1, 17.65 parts of Bisphenol A, 33.72 parts of tall oil fatty acids and 6.85 parts of dimer acids as described in Example 1. The resulting ester, when dissolved at 50 percent solids in xylene, had a Gardner-Holdt viscosity at 25° C. of X-Y.
- a clear coating composition was prepared from the epoxy ester solution of Example 1 by adding cobalt naphthenate and manganese naphthenate driers in the amount of about 0.156 percent cobalt and 0.078 percent manganese, both as metal based on ester solids. The solution was reduced to 70 percent solids with xylene to an application viscosity of 76 KU s .
- a clear coating composition was also prepared from Example 2. Reduction to application viscosity of 89 KU s was 41.2 percent solids.
- Films prepared from the coating composition made from Example 1 were tracked free in 6 to 24 hours and developed a pencil hardness of less than 6B in two weeks.
- the solvent resistance, methyl ethyl ketone double rubs, was 12 after two weeks.
- Comparable films made from the Example 2 epoxy ester were tack free in 3 hours and developed pencil hardness of HB after two weeks.
- the solvent resistance after two weeks was 6 methyl ethyl ketone double ribs.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Abstract
Description
Claims (9)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/122,060 US4786666A (en) | 1987-11-18 | 1987-11-18 | Epoxy compositions containing glycidyl ethers of fatty esters |
CA000581708A CA1328529C (en) | 1987-11-18 | 1988-10-31 | Epoxy ester compositions |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/122,060 US4786666A (en) | 1987-11-18 | 1987-11-18 | Epoxy compositions containing glycidyl ethers of fatty esters |
Publications (1)
Publication Number | Publication Date |
---|---|
US4786666A true US4786666A (en) | 1988-11-22 |
Family
ID=22400369
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/122,060 Expired - Fee Related US4786666A (en) | 1987-11-18 | 1987-11-18 | Epoxy compositions containing glycidyl ethers of fatty esters |
Country Status (2)
Country | Link |
---|---|
US (1) | US4786666A (en) |
CA (1) | CA1328529C (en) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0379943A2 (en) * | 1989-01-23 | 1990-08-01 | The Dow Chemical Company | Process for preparation of high-molecular-weight epoxy dimer acid ester resin |
US5059293A (en) * | 1988-12-13 | 1991-10-22 | Kansai Paint Co., Ltd. | Coating resin composition |
US5070174A (en) * | 1989-04-28 | 1991-12-03 | The Dow Chemical Company | Polyamide epoxy ester resin, process for preparation thereof and coating composition |
US5162490A (en) * | 1989-06-06 | 1992-11-10 | Schering Ag | Polyamide resins based on dimerized fatty acids, process for producing them, and process for manufacturing printing inks by the use of said polyamide resins |
US5223558A (en) * | 1990-01-22 | 1993-06-29 | The Dow Chemical Company | Process for preparation of high-molecular-weight epoxy dimer acid ester resin |
EP0555589A1 (en) * | 1992-02-10 | 1993-08-18 | Shell Internationale Researchmaatschappij B.V. | Vernonia oil modification of epoxy resins |
WO1994022954A1 (en) * | 1993-03-30 | 1994-10-13 | Shell Internationale Research Maatschappij B.V. | Epoxidized vegetable oil modification of epoxy esters |
US5391652A (en) * | 1992-09-30 | 1995-02-21 | The Dow Chemical Company | High molecular weight epoxy ester resin composition, process therefor and coating composition |
US5789039A (en) * | 1994-09-06 | 1998-08-04 | Herberts Powder Coatings, Inc. | Radiation curing of powder coatings on heat sensitive substrates: chemical compositions and processes for obtaining coated workpieces |
US5877231A (en) * | 1994-04-20 | 1999-03-02 | Herberts Powder Coatings, Inc. | Radiation curable powder coatings for heat sensitive substrates |
WO2000000533A1 (en) * | 1998-06-26 | 2000-01-06 | Vantico Ag | Heat-curable can-coating lacquer |
KR100587480B1 (en) * | 2005-05-06 | 2006-06-09 | 국도화학 주식회사 | Epoxy modified with alcoxysilane |
US20070298976A1 (en) * | 2006-06-09 | 2007-12-27 | David Antony Ballard | Surfactant materials and coatings for weighting agents for use in oil based drilling fluids |
US20110039981A1 (en) * | 2008-05-22 | 2011-02-17 | Hefner Robert E | Epoxy resins derived from non-seed oil based alkanolamides and a process for preparing the same |
US20110046321A1 (en) * | 2008-05-22 | 2011-02-24 | Earls Jim D | Adducts of epoxy resins derived from alkanolamides and a process for preparing the same |
US20110060076A1 (en) * | 2008-05-22 | 2011-03-10 | Hefner Jr Robert E | Epoxy resins derived from seed oil based alkanolamides and a process for preparing the same |
CN104364288A (en) * | 2012-06-11 | 2015-02-18 | 陶氏环球技术有限公司 | Low-viscosity phenolic diglycidyl ethers for epoxy coating applications |
WO2023034101A1 (en) | 2021-09-01 | 2023-03-09 | Ingevity South Carolina, Llc | Bio-based resin, curable composition and polyurethane based thereon, and related methods |
US11802176B2 (en) | 2019-11-08 | 2023-10-31 | Ingevity South Carolina, Llc | Bio-based epoxy resins, compositions, and methods thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3138566A (en) * | 1960-01-08 | 1964-06-23 | Gen Mills Inc | Fluid resins prepared from epoxidized unsaturated fatty acids or esters |
US3351574A (en) * | 1965-02-24 | 1967-11-07 | Celanese Coatings Co | Castor oil polyglycidyl ether |
US4040994A (en) * | 1976-11-26 | 1977-08-09 | Unitech Chemical Inc. | Cured epoxy resins |
-
1987
- 1987-11-18 US US07/122,060 patent/US4786666A/en not_active Expired - Fee Related
-
1988
- 1988-10-31 CA CA000581708A patent/CA1328529C/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3138566A (en) * | 1960-01-08 | 1964-06-23 | Gen Mills Inc | Fluid resins prepared from epoxidized unsaturated fatty acids or esters |
US3351574A (en) * | 1965-02-24 | 1967-11-07 | Celanese Coatings Co | Castor oil polyglycidyl ether |
US4040994A (en) * | 1976-11-26 | 1977-08-09 | Unitech Chemical Inc. | Cured epoxy resins |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5059293A (en) * | 1988-12-13 | 1991-10-22 | Kansai Paint Co., Ltd. | Coating resin composition |
EP0379943A2 (en) * | 1989-01-23 | 1990-08-01 | The Dow Chemical Company | Process for preparation of high-molecular-weight epoxy dimer acid ester resin |
EP0379943A3 (en) * | 1989-01-23 | 1990-11-28 | The Dow Chemical Company | Process for preparation of high-molecular-weight epoxy dimer acid ester resin |
US5070174A (en) * | 1989-04-28 | 1991-12-03 | The Dow Chemical Company | Polyamide epoxy ester resin, process for preparation thereof and coating composition |
US5162490A (en) * | 1989-06-06 | 1992-11-10 | Schering Ag | Polyamide resins based on dimerized fatty acids, process for producing them, and process for manufacturing printing inks by the use of said polyamide resins |
US5223558A (en) * | 1990-01-22 | 1993-06-29 | The Dow Chemical Company | Process for preparation of high-molecular-weight epoxy dimer acid ester resin |
EP0555589A1 (en) * | 1992-02-10 | 1993-08-18 | Shell Internationale Researchmaatschappij B.V. | Vernonia oil modification of epoxy resins |
US5391652A (en) * | 1992-09-30 | 1995-02-21 | The Dow Chemical Company | High molecular weight epoxy ester resin composition, process therefor and coating composition |
WO1994022954A1 (en) * | 1993-03-30 | 1994-10-13 | Shell Internationale Research Maatschappij B.V. | Epoxidized vegetable oil modification of epoxy esters |
CN1046749C (en) * | 1993-03-30 | 1999-11-24 | 国际壳牌研究有限公司 | Epoxidized vegetable oil modification of epoxy esters |
US5877231A (en) * | 1994-04-20 | 1999-03-02 | Herberts Powder Coatings, Inc. | Radiation curable powder coatings for heat sensitive substrates |
US5935661A (en) * | 1994-09-06 | 1999-08-10 | Herberts Powder Coatings, Inc. | Radiation curing of powder coatings on heat sensitive substrates: chemical compositions and processes for obtaining coated workpieces |
US5789039A (en) * | 1994-09-06 | 1998-08-04 | Herberts Powder Coatings, Inc. | Radiation curing of powder coatings on heat sensitive substrates: chemical compositions and processes for obtaining coated workpieces |
WO2000000533A1 (en) * | 1998-06-26 | 2000-01-06 | Vantico Ag | Heat-curable can-coating lacquer |
KR100587480B1 (en) * | 2005-05-06 | 2006-06-09 | 국도화학 주식회사 | Epoxy modified with alcoxysilane |
US20070298976A1 (en) * | 2006-06-09 | 2007-12-27 | David Antony Ballard | Surfactant materials and coatings for weighting agents for use in oil based drilling fluids |
US8178475B2 (en) * | 2006-06-09 | 2012-05-15 | M-I L.L.C | Surfactant materials and coatings for weighting agents for use in oil based drilling fluids |
US20110039981A1 (en) * | 2008-05-22 | 2011-02-17 | Hefner Robert E | Epoxy resins derived from non-seed oil based alkanolamides and a process for preparing the same |
US20110046321A1 (en) * | 2008-05-22 | 2011-02-24 | Earls Jim D | Adducts of epoxy resins derived from alkanolamides and a process for preparing the same |
US20110060076A1 (en) * | 2008-05-22 | 2011-03-10 | Hefner Jr Robert E | Epoxy resins derived from seed oil based alkanolamides and a process for preparing the same |
CN104364288A (en) * | 2012-06-11 | 2015-02-18 | 陶氏环球技术有限公司 | Low-viscosity phenolic diglycidyl ethers for epoxy coating applications |
US11802176B2 (en) | 2019-11-08 | 2023-10-31 | Ingevity South Carolina, Llc | Bio-based epoxy resins, compositions, and methods thereof |
WO2023034101A1 (en) | 2021-09-01 | 2023-03-09 | Ingevity South Carolina, Llc | Bio-based resin, curable composition and polyurethane based thereon, and related methods |
Also Published As
Publication number | Publication date |
---|---|
CA1328529C (en) | 1994-04-12 |
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Legal Events
Date | Code | Title | Description |
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AS | Assignment |
Owner name: INTEREZ, INC., A CORP. OF GA,KENTUCKY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CECIL, JOSEPH L.;KURNIK, WALTER J.;BABCOCK, DONALD E.;SIGNING DATES FROM 19871116 TO 19871118;REEL/FRAME:004782/0499 Owner name: INTEREZ, INC., 10100 LINN STATION RD., LOUISVILLE, Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:CECIL, JOSEPH L.;KURNIK, WALTER J.;BABCOCK, DONALD E.;REEL/FRAME:004782/0499;SIGNING DATES FROM 19871116 TO 19871118 |
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Owner name: HI-TEK POLYMERS, INC. A CORP. OF GA Free format text: MERGER;ASSIGNOR:INTEREZ, INC. (MERGED INTO);REEL/FRAME:006136/0781 Effective date: 19880725 Owner name: HI-TEK POLYMERS, INC., KENTUCKY Free format text: MERGER;ASSIGNOR:INTEREZ, INC.;REEL/FRAME:006136/0781 Effective date: 19880725 |
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Owner name: SHELL OIL COMPANY, TEXAS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HI-TEK POLYMERS, INC.;REEL/FRAME:007082/0029 Effective date: 19930330 |
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LAPS | Lapse for failure to pay maintenance fees | ||
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 19961127 |
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Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |